CN112341466A - Organic compound and organic light-emitting device using same - Google Patents
Organic compound and organic light-emitting device using same Download PDFInfo
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Abstract
The present invention provides an organic compound and an organic light emitting device using the same, and more particularly, to a soluble organic compound having excellent color purity and high brightness and light emitting efficiency and an OLED device using the same. The structure of the organic compound provided by the invention is shown as formula 1:
in the above structural formula, Ar1And Ar2Each independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstitutedA C10-C30 fused ring group, a substituted or unsubstituted C8-C30 heteroaryl group, a substituted or unsubstituted C13-C30 amine derivative, or a fluorene derivative; z represents a substituted or unsubstituted naphthalene derivative.
Description
Technical Field
The present invention relates to an organic compound and an organic light emitting tube device using the same, and more particularly, to a soluble organic compound having excellent color purity and high luminance and light emitting efficiency and an OLED device using the same.
Background
With the development of multimedia technology and the increase of information-oriented requirements, the requirements for the performance of panel displays are increasing. The OLED has a series of advantages of autonomous light emission, low-voltage direct current driving, full curing, wide viewing angle, rich colors and the like, is widely noticed due to potential application in new-generation displays and lighting technologies, and has a very wide application prospect. The organic electroluminescent device is a spontaneous light emitting device, and the OLED light emitting mechanism is that under the action of an external electric field, electrons and holes are respectively injected from a positive electrode and a negative electrode and then migrate, recombine and attenuate in an organic material to generate light. A typical structure of an OLED comprises one or more functional layers of a cathode layer, an anode layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport layer, a hole injection layer and an organic light emitting layer.
Although the research on organic electroluminescence is rapidly progressing, there are still many problems to be solved, such as the improvement of External Quantum Efficiency (EQE), the design and synthesis of new materials with higher color purity, the design and synthesis of new materials with high efficiency electron transport/hole blocking, and the like. For the organic electroluminescent device, the luminous quantum efficiency of the device is the comprehensive reflection of various factors and is an important index for measuring the quality of the device.
Luminescence can be divided into fluorescence and phosphorescence. In fluorescence emission, an organic molecule in a singlet excited state transits to a ground state, thereby emitting light. On the other hand, in phosphorescence, organic molecules in a triplet excited state transition to a ground state, thereby emitting light.
At present, some organic electroluminescent materials have been commercially used due to their excellent properties, but as host materials in organic electroluminescent devices, it is more important to have good hole transport properties in addition to the triplet energy level higher than that of the guest materials to prevent the energy reverse transfer of exciton transition release. Currently, materials having both a high triplet level and good hole mobility in the host material are still lacking. Therefore, how to design a new host material with better performance is a problem to be solved by those skilled in the art.
Disclosure of Invention
An object of the present invention is to provide an organic compound having excellent pure chromaticity, high luminance and excellent luminous efficiency, and an organic light emitting device using the same
The invention provides an organic compound, the structural formula of which is shown as 1,
in the above structural formula, Ar1And Ar2Each independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C10-C30 condensed ring group, substituted or unsubstituted C8-C30 heteroaryl, substituted or unsubstituted C13-C30 amine derivative or fluorene derivative; z represents a substituted or unsubstituted naphthalene derivative.
Preferably, an organic compound characterized by: the structural formula is shown as I-1-I-15:
a and B are independently selected from substituted or unsubstituted benzofuran, benzothiophene, 1-dialkyl-1H-indene, 2, 3-benzopyrrole, benzo [ B [, B [ ]]Silanes, benzothiazines, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted
A group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted naphthyridinyl group, or a combination thereof;
R1、R2and R3Each independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C10-C30 condensed ring group, substituted or unsubstituted C8-C30 heteroaryl, substituted or unsubstituted C13-C30 amine derivative or fluorene derivative; z represents a substituted or unsubstituted naphthalene derivative.
In a further preferred embodiment, the pyrimidine complexes A and B in the structure of the organic compound are independently selected from the following structures:
wherein R is4、R5、R6Independently selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 nitrogen-containing heteroaryl, or the combination thereof.
In a further preferred manner, the organic compounds are independently selected from the following compounds:
the invention also provides application of the carbazole series-containing compound in an organic light-emitting device.
Preferably, the organic light emitting device includes an anode, a cathode, and a plurality of organic functional layers located between the anode and the cathode, where the organic functional layers contain the compound containing carbazole series.
The invention has the beneficial effects that:
the invention provides a carbazole series-containing compound, which has a structure shown in a formula 1, wherein an electron-rich structure in the carbazole series compound has great influence on the photoelectric property of the whole compound molecule, so that unnecessary vibration energy loss is reduced, and high-efficiency luminous performance is realized. By adjusting substituent groups, the compound has better thermal stability and chemical properties. The compound containing carbazole series has the advantages of simple preparation method and easily obtained raw materials, and can meet the industrial requirements.
The carbazole series compounds are prepared into devices, particularly used as main materials, the devices have the advantages of low driving voltage and high luminous efficiency, and are superior to the conventional common OLED devices.
In the present invention, the organic electroluminescent device preferably includes an anode, a cathode, and several organic layers located between the anode and the cathode, and the "organic layer" refers to a term of all layers disposed between the anode and the cathode in the organic electroluminescent device. The organic layer may be a layer having a hole characteristic and a layer having an electron characteristic. For example, the organic layer includes one or more of a hole injection layer, a hole transport layer, a technical layer having both hole injection and hole transport, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a technical layer having both electron transport and electron injection.
In the present invention, the hole injection layer, the hole transport layer, and the functional layer having both hole injection and hole transport properties may be formed using a conventional hole injection material, a hole transport material, or a material having both hole injection and hole transport properties, and may further include a material for generating electrons.
For example, the organic layer includes a light emitting layer, and the light emitting layer includes one or more of a phosphorescent host, a fluorescent host, a phosphorescent dopant, and a fluorescent dopant. In the present invention, the compound for an organic electroluminescent device can be used as a fluorescent host, as a fluorescent dopant, and as both a fluorescent host and a fluorescent dopant.
In the present invention, the light emitting layer may be a red, yellow or blue light emitting layer. In the present invention, when the light-emitting layer is a light-emitting layer, an organic electroluminescent device having high efficiency, high resolution, high luminance and long life can be obtained by using the above-mentioned compound for an organic electroluminescent device as a host.
In the present invention, the organic electroluminescent diode device of the organic compound is characterized in that the organic electroluminescent diode device comprises an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode, which are sequentially deposited, and the organic compound is used as a host material of the light emitting layer.
The method for preparing the organic electroluminescent device is not particularly limited, and the organic electroluminescent device can be prepared by using the method and materials for preparing the light emitting device, which are well known to those skilled in the art, in addition to the organic compound of formula 1.
Drawings
FIG. 1 is a graph showing the relationship between luminance chromaticity and visibility of an organic electroluminescent diode according to the present invention.
Detailed Description
In order to make the technical means, the original characteristics, the achieved purposes and the effects of the invention easy to understand, the invention is further described with reference to the figures and the specific embodiments.
Example 1: synthesis of Compound III-7
1. Synthesis of intermediate Sub-1
A500 mL reaction flask was charged with intermediate Sub-0(20.45g,61.4mmol), 1-iodo-2-nitrobenzene (15.29g,61.4mmol), tetrakis (triphenylphosphine) palladium (5 mol%), K2CO3(17.0g,122.8mmol), 1, 4-dioxane (200mL) and water (50 mL). The reaction system is heated to 80 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product, which was then passed through a silica gel column to obtain intermediate Sub-1(15.11g, yield 75%). LC-MS: M/Z326.99 (M + H)+。
2. Synthesis of intermediate Sub-2
A250 ml reaction flask was charged with Sub-1(0.33g,0.98mmol), triethyl phosphite (0.25g,1.47mmol), nitrogen
The reaction was carried out overnight at 145 ℃ under protection. The reaction was stopped, cooled and 2M HCl was added, stirred to a full white color and extracted with a small amount of DCM. The organic phase was taken out by liquid separation and turned to oil. Silica funnel, DCM: PE ═ 1: and 3, flushing. The solvent was dried by spinning and recrystallized to give Sub-2 as a white powdery solid (0.24g, yield 82%). LC-MS: M/Z295.00 (M + H)+。
3. Synthesis of intermediate Sub-3
A250 mL three-necked flask was charged with intermediate Sub-2(5.92g, 20mmol), 9-iodophenanthrene (6.39g,21.0mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.8g,33.6mmol) and o-xylene (80 mL). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After the reaction is completed, the reaction solution is addedCooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product, which was then passed through a silica gel column to give Compound Sub-3(7.56g, yield 80%). LC-MS: M/Z471.06 (M + H)+。
4. Synthesis of intermediate Sub-4
A500 mL reaction flask was charged with 2-nitrophenylboronic acid (29.00g,61.4mmol), Sub-3(17.68g,61.4mmol), tetrakis (triphenylphosphine) palladium (5 mol%), K2CO3(17.0g,122.8mmol), 1, 4-dioxane (200mL) and water (50 mL). The reaction system is heated to 80 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product, which was then passed through a silica gel column to give an intermediate, Sub-4(22.12g, yield 70%). LC-MS: M/Z514.17 (M + H)+。
5. Synthesis of intermediate Sub-5
A250 ml reaction flask was charged with Sub-4(0.51g,0.98mmol), triethyl phosphite (0.25g,1.47mmol), nitrogen
The reaction was carried out overnight at 145 ℃ under protection. The reaction was stopped, cooled and 2M HCl was added, stirred to a full white color and extracted with a small amount of DCM. The organic phase was taken out by liquid separation and turned to oil. Silica funnel, DCM: PE ═ 1: and 3, flushing. The solvent was dried by evaporation and recrystallized to give Sub-5(0.38g, yield 80%). LC-MS: M/Z482.18 (M + H)+。
6. Synthesis of Compound 40
A250 ml three-necked flask was charged with intermediate Sub-5(9.65g, 20mmol), intermediate Sub-6(5.05g,21.0mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.8g,33.6mmol) and o-xylene (80 mL). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product, which was then passed through a silica gel column to obtain Compound III-7(10.85g, yield 79%). LC-MS: M/Z686.25 (M + H)+。
Example 2: synthesis of Compound III-61
Compound III-61 was synthesized by the method described in reference example 1, and the other steps referred to the synthesis of compound III-7 to give compound III-61(8.71g, yield 75%). LC-MS: M/Z869.35 (M + H)+。
Example 3: synthesis of Compound III-102
Compound III-102 was synthesized by the method described in reference example 1, and the other steps referred to the synthesis of compound III-7 to give compound III-102(7.76g, yield 72%). LC-MS: M/Z870.31(M + H)+。
Example 4: synthesis of Compound II-1
Compound II-1 was synthesized by the method described in reference example 1, and the other steps referred to the synthesis of Compound III-7 to give Compound II-1(8.75g, yield 70%). LC-MS: M/Z714.25(M + H)+。
Example 5: synthesis of Compound II-55
Compound II-55 was synthesized by the method described in reference example 1, and the other steps referred to the synthesis of Compound III-7, to give Compound II-55(7.83g, yield 65%). LC-MS: M/Z826.20(M + H)+。
Example 6: synthesis of Compound II-85
Compound II-85 was synthesized by the method described in reference example 1, and the other steps referred to the synthesis of Compound III-7, to give Compound II-85(6.57g, yield 60%). LC-MS: M/Z714.25(M + H)+。
Example 7: synthesis of Compound IV-1
Compound IV-1 was synthesized by the method described in reference example 1, and the other steps referred to the synthesis of Compound III-7 to give Compound IV-1(6.65g, yield 80%). LC-MS: M/Z865.35 (M + H)+。
Example 8: synthesis of Compound IV-6
Compound IV-6 was synthesized by the method described in reference example 1, and the other steps referred to the synthesis of Compound III-7 to give Compound IV-6(6.61g, yield 61%). LC-MS: M/Z815.29 (M + H)+。
Example 9: synthesis of Compound IV-36
Process cartridge according to reference example 1The compound III-36 was obtained, and the other steps referred to the synthesis of the compound III-7, to obtain the compound IV-36(9.26g, yield 78%). LC-MS: M/Z775.30 (M + H)+。
Example 10: synthesis of Compound II-14
Compound II-14 was synthesized by the method described in reference to example 1, and the synthesis of example 2 was referred to for the other steps to obtain Compound II-14(16.15g, yield 85%). LC-MS: M/Z814.28(M + H)+。
Example 11: synthesis of Compound II-20
Compound II-20 was synthesized by the method described in reference to example 1, and the synthesis of example 2 was referred to for the other steps to obtain Compound II-20(17.52g, yield 81%). LC-MS: M/Z7914.05(M + H)+。
Evaluation example 1: HOMO, LUMO, triplet energy level, and S1-T1 energy level evaluation of the compounds:
the data show that when electron-donating groups exist in the carbazole series compounds, the difference between the singlet state and the triplet state is obviously smaller than that of the electron-withdrawing group compounds. This can improve the light emission efficiency of the light emitting layer.
Device embodiments
(I) Evaluation of luminescent Material devices
The compounds of the respective organic layers used in the device examples are as follows:
device embodiments
1. First embodiment
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. The patterned ITO glass substrate was then washed.
The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-5And (6) handkerchief. Thereafter on an ITO substrate
Compound (I)
ET-1(50 wt.%) and
and
the sequence of (a) and (b) forming layers of organic material.
2. Second embodiment
An organic light-emitting device of the second embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound III-61 from compound III-7 of the first embodiment.
3. Third embodiment
An organic light-emitting device of the third embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound III-102 instead of the compound III-7 of the first embodiment.
4. Fourth embodiment
An organic light-emitting device of the fourth embodiment was prepared in the same manner as in the first embodiment above, except that the host material layer of the organic light-emitting device was replaced with compounds II-1 and IV-1(1:1 mixture) instead of compound III-7 of the first embodiment.
5. Fifth embodiment
The organic light-emitting device of the fifth embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compounds II-55 and IV-6(1:1 mixture) from the compound III-7 of the first embodiment.
6. Sixth embodiment
The organic light-emitting device of the fifth embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compounds II-85 and IV-36(1:1 mixture) instead of the compound III-7 of the first embodiment.
7. Comparative example 1
An organic light-emitting device of comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound RH-a from the compound III-7 of the first embodiment.
8. Comparative example 2
An organic light-emitting device of comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound RH-B from the compound III-7 of the first embodiment.
9. Comparative example 3
An organic light-emitting device of comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound RH-C from the compound III-7 of the first embodiment.
10. Comparative example 4
An organic light-emitting device of comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compounds RH-C and RH-B (1:1 mixture) from the compound III-7 of the first embodiment.
11. Comparative example 5
An organic light-emitting device of comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compounds RH-D and RH-B (1:1 mixture) from the compound III-7 of the first embodiment.
The prepared organic light-emitting device is at 10mA/cm2Voltage, efficiency and life were tested under current conditions.
Table 1 shows the performance test results of the organic light emitting devices prepared in the examples of the present invention and the comparative examples.
TABLE 1
As shown in table 1, the device also operated efficiently at low voltage. And the current efficiency and the lifespan of the embodiment were significantly increased as compared to the comparative example.
(II) evaluation of Electron transporting Material device
The compounds of the respective organic layers used in the device examples are as follows:
12. seventh embodiment
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. The patterned ITO glass substrate was then washed. The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-5And (6) handkerchief. Thereafter on an ITO substrate
BH (95 wt)% and
II-7 (50% by weight) and
and
the sequence of (a) and (b) forming layers of organic material.
13. Eighth embodiment
An organic light-emitting device of the ninth embodiment was fabricated by the same method as that of the seventh embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound II-11 from compound II-7 of the first embodiment.
14. Comparative example 6
An organic light-emitting device of comparative example was prepared in the same manner as in the above-described seventh embodiment, except that the host material layer of the organic light-emitting device was replaced with ET-1 instead of compound II-7 of the first embodiment.
15. Comparative example 7
An organic light-emitting device of comparative example was fabricated by the same method as in the seventh embodiment above, except that the host material layer of the organic light-emitting device was replaced with ET-2 instead of compound II-7 of the first embodiment.
TABLE 2
As shown in Table 2, the current efficiency and lifetime of the prior art ET-1 and ET-2 are significantly increased over the embodiments when the compound of the present invention is used as an electron transport material.
The foregoing has described the general principles, principal features, and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are given by way of illustration of the principles of the present invention, and that various changes and modifications may be made without departing from the spirit and scope of the invention as defined by the appended claims. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (10)
1. An organic compound characterized by: the structural formula is shown as 1:
in the above structural formula, Ar1And Ar2Each independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C10-C30 condensed ring group, substituted or unsubstituted C8-C30 heteroaryl, substituted or unsubstituted C13-C30 amine derivative or fluorene derivative; z represents a substituted or unsubstituted naphthalene derivative.
2. An organic compound characterized by: the structural formula is shown as I-1-I-15:
wherein A and B are independently selected from substituted or unsubstituted benzofuran, benzothiophene, 1-dialkyl-1H-indene, 2, 3-benzopyrrole, benzo [ B [, B [ ]]Silanes, benzothiazines, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted
A substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted phenanthroline group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted naphthyridinyl group, or a combination thereof;
R1、R2and R3Each independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C10-C30 condensed ring group, substituted or unsubstituted C8-C30 heteroaryl, substituted or unsubstitutedA substituted C13-C30 amine derivative or fluorene derivative; z represents a substituted or unsubstituted naphthalene derivative.
3. An organic compound according to claim 1, wherein the pyrimidine complexes A and B are independently selected from the group consisting of:
wherein R is4、R5、R6Independently selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 nitrogen-containing heteroaryl, or the combination thereof.
4. The organic compound according to any one of claims 1 to 3, wherein: the organic compound is independently selected from the following compounds:
5. an organic electroluminescent diode device using the organic compound according to any one of claims 1 to 4, characterized in that: the organic electroluminescent device sequentially comprises a deposited anode, a hole injection layer, a hole transport layer, a luminescent layer, an electron transport layer, an electron injection layer and a cathode, wherein the organic compound is used as a main material of the luminescent layer.
6. The organic photoelectric element according to claim 5, wherein the compound according to any one of claims 1 to 4 is used alone or in combination with other compounds.
7. The organic optoelectronic component according to claim 5, wherein the compound according to claims 1 to 4 is used as an electron blocking layer.
8. The organic photoelectric element according to claim 5, wherein the compound according to any one of claims 1 to 4 is used as a light-emitting layer or an active layer.
9. The organic photoelectric element according to claim 5, wherein the compound according to claim 1 to 4 is used as a hole-blocking layer.
10. The organic photovoltaic element according to claim 5, wherein the compound according to any one of claims 1 to 4 is used as an electron transporting layer.
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